2-Methylpiperazine → HCID 20099357, compound

HRID 1626312Notes

Reaction equation

HRID 1626312 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[CH3:16].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][C:10]1[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:9]=1[N:6]1[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[CH2:7]1

Participants

7

Reactant 4

HCID 660572-MethylpiperazineHCID 684723-Bromo-o-xyleneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 20099357HCID 20099357, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

650 mg (6.48 mmol) of 2-methylpiperazine, 800 mg (4.32 mmol) of 3-bromo-o-xylene, 50 mg (0.22 mmol) of palladium acetate, 110 mg (0.17 mmol) of BINAP and 830 mg (8.65 mmol) of sodium tert-butoxide in dry toluene (8.6 mL) were heated at 110° C. for 14 hours. After cooling, the resulting reaction mixture was quenched with water and extracted with ethyl acetate. The ethyl acetate phase was concentrated. The residue was purified by chromatography to give the title compound as a yellow semi solid.

Workup

  1. temperatureAfter cooling
  2. customthe resulting reaction mixture
  3. customwas quenched with water
  4. extractionextracted with ethyl acetate
  5. concentrationThe ethyl acetate phase was concentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-f3d7dbdf8939441ab1f305ae69f61051
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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